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[ CAS No. 1262320-50-2 ] {[proInfo.proName]}

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Chemical Structure| 1262320-50-2
Chemical Structure| 1262320-50-2
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Product Details of [ 1262320-50-2 ]

CAS No. :1262320-50-2 MDL No. :
Formula : C16H19BrFN3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 384.24 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1262320-50-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1262320-50-2 ]

[ 1262320-50-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 153505-37-4 ]
  • [ 15761-39-4 ]
  • [ 1262320-50-2 ]
YieldReaction ConditionsOperation in experiment
Intermediate 15: Step ITo a cold (0-4 C) solution of 4-bromo-5-fluoro-benzene-1 ,2-diamine (1 g, 4.877 mmol) and (2S)-1 -tert-butoxycarbonylpyrrolidine-2-carboxylic acid (Boc-Pro-OH) (1.050 g, 4.877 mmol) in DMF (9.754 mL) are sequentially added HATU (2.040 g, 5.365 mmol) and 2,4,6-collidine (886.5 mg, 966.7 mul_, 7.316 mmol). The reaction mixture is slowly warmed up to rt, stirred overnight, and diluted with water (20 mL). The resulting suspension is extracted with EtOAc(3 x 25 mL), and the combined extracts are washed with saturated bicarbonate solution, and brine. The organic phase is dried over sodium sulfate, and concentrated under vacuum to give crude amide (2.35 g, contaminated with 2,4,6-collidine). The residue is dissolved in acetic acid (15 mL), stirred at 50 C for 8 h, and concentrated to dryness. The residue is diluted with ethyl acetate (25 mL), washed with aq. NaHCO3 solution, and brine. The organic phase is dried over sodium sulfate, concentrated under vacuum and the residue is purified by silica gel chromatography (ethyl acetate/hexanes,40 to 60 %) to give 15 (1.74 g) as light brown solid.1 H NMR spectra in CDCl 3 and CD 3 OD showed 1.2:1 and 2:1 ratio of isomeric mixture (exchange of imidazole nitrogen) .19F spectra also showed mixture of two isomers. 1H NMR (400 MHz, CDCl3, 1.2:1 ratio of isomers): Peaks for the major isomer, delta [ppm] 7.86 (d, J = 6.2, 1 H), 7.45 (d, J = 9.2, 1 H), 6.77(s, 0.35 H), 5.02 (m, 1 H), 3.41 (m, 2 H), 2.2-1.9 (m, 2 H), 1.49 (s, 3 H). LC/MS: m/z = 303.78 (M-100+H+). 19F NMR (400 MHz, CDC13), delta [ppm] -113.4 (t), -115.7 (t).
Reference： [1]Patent: WO2011/9084,2011,A2 .Location in patent: Page/Page column 352
  • 2
  • [ 153505-36-3 ]
  • [ 1262320-50-2 ]
Reference： [1]Patent: WO2012/83170,2012,A1
  • 3
  • [ 153505-37-4 ]
  • [ 15761-39-4 ]
  • [ 1262320-50-2 ]
YieldReaction ConditionsOperation in experiment
77% Illustration of General Procedure 20. General Procedure 20A; (S)-tert-buty 2-(6-bromo-5-fluoro-l f-benzo[i/]imidazol-2-yl)pyrrolidine-l-carboxylate; To a solution of 4-bromo-5-fluorobenzene-l,2-diamine (1.7 g, 8.4 mmol) in DMSO (42 mL) was added (.S)-l-(ieri-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.8 g, 8.4 mmol) followed by HATU (3.5 g, 9.3 mmol) and NNf Uisopropyl-N-ethylamine (3.7 mL, 21.1 mmol), and the solution was stirred for 16 hours. The reaction mixture was diluted with EtOAc, washed with H20 and brine, dried (Na2S04), filtered and concentrated. Acetic acid (40 mL) was added, and the mixture was stirred at 60 C for 4 hours. Then, the reaction mixture was cooled and concentrated. The residue was azeotroped 2 times with toluene to give crude product which was purified by flashchromatography (0-50% EtOAc/hexane) to give the title compound (2.5g, 6.4 mmol, 77%).
Reference： [1]Patent: WO2012/83170,2012,A1 .Location in patent: Page/Page column 158
[2]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5462 - 5467

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